


Deans Alternate Incum

by bellabri287



Category: Supernatural
Genre: Anal Fingering, Dean in Panties, Exhibitionism, I'm Bad At Tagging, M/M, Masturbation, Men of Letters Bunker, My First Fanfic, Sex Toys, Voyeurism
Language: English
Status: In-Progress
Published: 2017-01-22
Updated: 2017-01-22
Packaged: 2018-09-19 06:17:37
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 3,676
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/9422204
Author URL: https://archiveofourown.org/users/bellabri287/pseuds/bellabri287
Summary: Excuse the title, its terrible but i cannot think of anything clever.Please be gentle with me!  This is my first fanfic, I am usually one to come up with imagines and ideas and feed them to my beautiful fanfic writer friends but I chose to keep this one and try writing.  I read a DCBB2016 fic about an AU Dean being a cam boy to get through marketing school.  It was so hot that I wanted to write a fic that is canon based, Dean cams for money unbeknownst to Sam & Cas.  Destiel smut ensues.Thank you to the beautiful Piper_Halliwell1979 for giving this a once over before I posted.





	

CHAPTER 1   
~~~~~~~~~~~~~~~~~~~~~~~~~~~~~

  
Dean finished cleaning the cum off his chest with a damp towel. He took a peek at his tip count for the night, $750 not bad at all. He washed off the sparkly blue dildo with antibacterial soap and put that and his bottle of Astroglide in the box under his bed. One awesome orgasm and little over an hour and half of his time not a bad night's work. The amount of money he could make by camming was awesome and easy.  He flopped on to his bed, got under the covers and let himself slip into blissful post orgasmic sleep.   
~~~~~~~~~~~~~~~~~~~~~~~~~~~~~

  
Dean had learned over the years all the ways he could make quick and easy money. Of course his dad taught him cards, pool and darts. Those had been honed for years, he passed them on to Sammy and even gave Cas a few lessons when he was human to help him get by.  Sometimes though, when Sammy was off at college and he and Dad decided to do separate cases he just couldn’t pull in enough to fill his Baby.  He was no stranger to hookers, hell he competed with them for cash most nights. Unfortunately for Dean a man was much more likely to pay for a blowie in the bathroom than bet on pool.  Dean liked sex, he wasn’t too particular about who it was with either and he knew he could earn much more doing that than hustling at the bar. So, he began selling himself.   
  
There were never many female takers in the bars he frequented but there were plenty of guys looking for a pretty mouth to use. Dean got really good at sucking cock.  He learned what how far he would go for a hand job or straight blowie, he charged extra for things like swallowing and assplay.  Eventually he met a john who wasn’t content with using his hands or mouth, he wanted Dean's ass.  Dean was nervous as hell but the guy offered $500 for it and he needed the money, that’s how he lost his virginity with a dude.  From then on he hooked for money as often as he could when he wasn’t with Dad.  He found himself enjoying sex when he was with a good looking guy and some even took pleasure in making him cum.  He found himself more of a switch and when he found a gay bar always cruised as a top as most regular bar johns only wanted his hole or his mouth.  He kept on hooking and was able to sustain himself to keep hunting solo. Until Dad didn’t come back and he had to get Sammy.  That put a freeze on things indefinitely, he didn’t want Dad or Sammy to know about his alternate source of income.   
  
Then he died. Cas brought him back and the Apocalypse happened. Life was a mess and he had returned to hustling cards, pool and darts to get by.  It was only when he could be SURE to get away from Sammy & Cas that he would sneak out to the gay bars, which he found more frequently these days, and get a few johns.  When he went darkside and became a Demon he stopped charging, just looked for hookups.  On many occasions he was told he could do porn and make boatloads of money. Dean Winchester was no stranger to porn, not in the slightest and while he didn’t want to do professional porn he was not opposed to performing in front of a camera.  He frequented cam sites himself and decided to try his hand on the other side. He didn’t need sleep so he started his own channel on a couple different sites, gay and straight.  Dean cleared $200 his first night with some dirty talk, showing off his junk, a little assplay and a private chatroom tugjob.   
  
He kept camming, hiding it from everyone.  He could easily do it in his room in the bunker privately and over the couple years he had been doing it he built up a small arsenal of things his subscribers had come to like.  He even did some videos out on the road for subscribers, sometimes outside or in Baby. He would wear panties on hunts sometimes for extra money, who knew he had a little bit of an exhibitionist kink.  Cam time was one of his favorite times, he could enjoy himself, explore himself and get attention from hundreds of guys. Over the few years he had been doing this he found he got more money on the gay sites than anything so he exclusively cammed there.  He had done things he never thought he would do for his paid subscribers, though he always made the most when he wore his panties and used one of his toys.  He had to keep them locked in a black box under his bed to make sure nobody would find out how he brought in extra money.  Dean wasn’t embarrassed about his source of extra income, he just didn’t want to have to explain to Sam and Cas.  At least he wasn’t hooking anymore right?   
~~~~~~~~~~~~~~~~~~~~~~~~~~~~~

  
Castiel was no stranger to human bodily functions.  While he was at full grace he could stop them indefinitely.  As his grace waned he began finding himself having more difficulty stifling bodily urges. Once human, with no grace to stop them he had to embrace his human body.  There were things he hated, urinating was obnoxious as was gas and defecating.  Eating was enjoyable but being hungry or thirsty was terrible.  Showering became a favorite pastime, the hot water was so soothing.  He found he had to clip his nails, get a haircut, blow his nose it was all so tiring and mundane. The first time he felt arousal was a surprise.  He had experienced an erection before, quite a few times he had allowed his body while watching pornography.  But as a human there was so much more to it.  The heat deep in his gut, the change in blood flow, and then touching himself was exquisite but he never had time to draw it out being homeless and living in the Gas & Sip.  He had lost his 'virginity' with April and experienced his first and several more orgasms.  While being taken advantage of by April had soiled his opinion of sex with a female she did not ruin everything.  Erections and masturbation were things Castiel decided he would not use his grace to stop once he had it back.    
  
That is how he found himself here.  Sitting in his bedroom at the bunker in his boxers with a painful erection.  The three of them had just returned home from a vamp nest clean out and he could not get to his room fast enough.  He had been in a constant state of arousal the entire drive home.  Just thinking about what he saw, what Dean was possibly wearing had Castiel more aroused than he had ever known before.   
~~~~~~~~~~~~~~~~~~~~~~~~~~~~~

  
“Hey Sammy you done burning those bodies?”   
“Yeah Dean, coming!”

  
Sam came lumbering up the small hill they had parked on, the charred remains of the vamp nest they just destroyed below.  Sam went around to the passenger side as Dean bent over to get the last of the gear back in Baby's trunk.  That's when Castiel saw the thin sliver of light blue satin & lace above Dean's jeans waistband.  Castiel stared, how could he not?  Those were not Deans underwear, those were not mens underwear. Castiel had seen Dean in his underwear many times while on the road sharing hotel rooms.  Why would he be wearing womens underwear?  The color looked beautiful on his freckled skin.  He must have stared too long because Dean's voice interrupted his thoughts.

  
“Cas? Whats up? You ready to go?”   
“Oh, um. Yes Dean, I am”   
“Okay… are you sure nothing's wrong? You were staring off into space there.”   
“I am fine Dean, let's go.”

  
He slid into the backseat of Baby and started their 4 hour drive home.  Castiel couldn’t shake the image of Dean in those light blue panties.  The only reason he could think Dean would wear them is because he wanted to.  Dean Winchester did not do anything he didn't want to do, but wanting to wear something so pretty and so feminine went against Dean's masculine bravado.  The more Castiel thought about it, the more he began to imagine the strip of light blue satin and lace he had seen.  The image changed to Dean without the jeans wearing the panties.  The thoughts had Castiel's cock quickly filling in his pant, his erection became painful the longer he thought about Dean in the panties. Castiel shifted in the back seat as quietly as possible to relieve himself of some of the ache in his groin.

  
“You okay back there Cas?”   
Castiel was lost for words, he was just imagining Dean fondling his own hardness through the panties and suddenly he was being spoken to. “Yes Dean I am fine.”   
“Okay, you are moving around an awful lot. Are you uncomfortable? We have about 30 min until we get home and you can stretch your legs.”   
“Okay Dean.” He really tried to be nonchalant but he was finding himself actually perturbed by his fantasy being interrupted.  He was anticipating their arrival home so he could relieve himself of the ache in his pants.

  
Castiel made sure he was the first one out of the car and sped to his room.  By then his erection had flagged a bit but he was still wanted to masturbate.  Fantasizing about Dean wasn’t new, but the panties were.  He wanted to see more, he needed to see more.  Dean had helped him navigate through pornography enough that he knew how to find what he wanted.  His laptop was flooded with pictures of men in panties, hard cocks, soft cocks, every style and every color.  He felt his erection come back with vigor and got comfortable on his bed.  He stripped to his boxers and placed his laptop off to the side.  As he scrolled through pictures he began to fondle himself, he felt like drawing this out after the simmering arousal he had for the last few hours.  He stroked through the neatly trimmed pubic hair at the base of his cock.  He preferred it short, something he found himself learning from YouTube videos he had watched on nights while the brothers slept.  He scrolled through the many pictures of men in lacy underwear and found himself wanting more.  He wanted to watch someone touch themselves and masturbate in a pair of panties.  He looked in his bookmarks and found a webcam site he frequented.

  
Since April he found his pornographic interests leaned more homoesexual. He typed in panties in the search options and found many channels.  By now he had removed his boxers and was slowly stroking himself from his balls to his tip, smearing the precum down.  His arousal was building as he looked at previews of who was live right now.  Then he saw a pair of light blue satin & lace panties.

  
Castiel logged into the show as fast as he could, his screen was filled with the image of a plump ass swaying in panties.  A pair of hands slowly caressed down the globes before they pulled the cheeks apart and gave them a smack.  This was what Castiel had been craving, he began to stroke himself with more intent. The panties were so similar to the ones he had seen Dean wearing it would be perfect to use as part of his masturbation fantasy.  The man on the screen turned around and Castiel saw the outline of a semi hardened cock under the light blue satin & lace. He noticed something else when the man turned, the background looked so familiar.  His focus became more on the background of the room the man was in, concrete looking walls and dated décor.  He could hear Styx playing quietly in the background as well as a shotgun on the wall above the man's bed.  The revelation hit Castiel only seconds before the man sat down in front of the camera to continue the show.

  
The gruff voice rung out through his laptop speakers “Hey boys, you ready to help me have some fun” He was watching Dean.   
~~~~~~~~~~~~~~~~~~~~~~~~~~~~~

  
Castiel sat up and stared at the screen, at the man he had saved from hell, his best friend, the unrequited love of his life.  Dean did webcam shows?  Why was he doing this on a gay cam site, Dean is not gay? Was this why he wore the panties?  Castiel's mind was racing but before he could begin to process anything Dean began talking again.

  
“So I see a lot of you like the light blue. Heheh, I hope my subscribers saw the snaps and little video I took of them today. I wore these during work and they were so smooth against my cock I had a hard time not popping a boner every time I moved the right way.”   
  


Castiel was entranced by the Dean he was seeing, a Dean he didn't know. The chat was moving rapidly as was the tip count. This explained what he had seen earlier, Dean was wearing panties for his cam subscribers.

  
“So boys, what do you want to see tonight?” Dean ran his fingers under the waistband of the panties and snapped them.   
“I plan on ruining these for sure, it's a shame to see them go but it feels so good to feel them slide around after you cum. Of course only my paid subscribers will get to see that.”   
  


Castiel fumbled around for his wallet to get a credit card and become a paid subscriber of Deans signing up with the username  **FallenAngel918** .  He watched as Dean spoke to some of the men in the chat, the way he spoke was like they were long time subscribers.  How long had Dean been doing this?  Before Castiel could finish his thought Dean began palming himself through the panties.   
  


_ Unf!  _ “So good, satin is always my favorite, though feel free to request any of types of panties you want to see me in. Who knows you might get lucky and I'll wear them.” Dean's cock was filling up quickly and Castiel's began to do the same.   
“It's been a long and rough few days, barely any time alone to play so this might be a quick show. Don't worry I'll do something longer next time.”   
  


Dean got up and turned around, stroking his ass and pulling the panties aside to expose his freckled ass. He bent over to give a small glimpse of his pink pucker as he pulled the panties down below his cheeks. He played with his ass before licking a finger and rubbing over his hole. The sounds coming from Dean on the laptop and the sight had Castiel's cock red, wanting, and leaking all over himself.  He had fantasized about the ass so many times and here it was in front of him on display.

  
_ Mmmph! _ “Love playing with my hole. I haven’t stuck anything in there all week do you guys want me to finger my ass?”   _ Hahahaha _ “well I'll take that as a yes seeing how the chat just exploded, thanks for the tips boys. Remember the main event ain't for free. The tip menu and cost for private shows is in my profile and posted here in the chat by my wonderful mods.”   
  


When Dean turned around and the tip of his cock was sticking out the side of the leg in the panties.  There were some smudges of precum on the satin leaving beautiful stains, Dean was obviously enjoying himself while he teased his hole.  This only caused Castiel to fondle himself more.  Dean  began rubbing his cock and pulled the panties down a bit to release it and his heavy balls. The head was glistening and Dean smeared his finger through the wetness sucking in a breath as he did.  Dean’s pubic hair was surprisingly reddish in color, sparse, neatly manicured leaving his balls free from hair.  Castiel watched on practically drooling at the up close sight on his laptop..    
  


“Okay guys I can't wait anymore, this is killing me I'm going to move to the paid room now follow me if you want to watch”

  
The screen went dark and Castiel quickly made sure to pay for entrance into the private room and waited. His screen was filled with Dean once again rubbing himself through the panties.

  
“I'm already so turned on guys welcome to the private room for those new subscribers.  Let's get this show started, I’ll try to respond to your chats but you know once I get going I can't stop.”  Dean gave a lascivious wink and settled back on his bed.

  
Castiel was captivated, running his hands over his torso and erection. Watching his best friend doing things Castiel would have never imagined Dean would do let alone that Castiel would see him do.

  
Dean was fully hard rubbing his plump cock through the panties. “I think we'll use this little guy tonight, what do you think boys?”   _ Hah  _ **“** well okay then!” 

 

Bringing out a glass prostate massager he rubbed it over his straining coak and balls then behind his balls, moaning the whole time.  He pulled the panties aside showing off his pink hole and began rubbing it with his fingers. Grabbing the bottle of Astrolgide, Dean slicks up his fingers and circles his entrance slowly staring into the camera and winking as he enters himself.  A full bodied moan and shudder escapes his mouth and Dean speaks in a voice huskier than before.

 

“Ah, fuck that’s nice. It's been too long guys”  _ Mmmph _ . He pumps the one finger in and out shifting so his leaking panty clad cock is obviously in view.  Eventually moving his leg up he slips a second finger in and begins to scissor as he pumps in and out.

 

Castiel's hand slides easily over his erection watching Dean on camera. It is so erotic knowing his best friend, his sexual fantasy for so long is doing this a few doors down. He feels the lust and arousal inside himself fighting to not lose control.

  
_ Nnnnngh! _ “I think that’s enough prep. Thanks boys I know you love to see my hole gape, next time though.  Who wants to watch my ass eat up this toy?”

 

Dean slicks up the glass toy and circles it around his hole before popping it in, moaning and grunting while he works it all the way in.  His face is the picture of pure pleasure as he moves the toy in and out slowly twisting and changing the angle as he moves it.  Once it makes contact with his prostate it's obvious by the jump and groan he makes.  He moves it in and out a while moaning and huffing small noises.  Deans cock strains against the panties and leaves precum smears all over the top of them.  He rearranges himself for a better view on camera, it’s obvious he has done this quite often.  Dean sits at an angle to prop the toy against the bed enough for him to fuck himself back on it.  He brings his weeping cock out of the top of the panties and begins to stroke with one hand and fondle his balls with the other while he fucks himself back on the toy.

  
Castiel can see beads of precum leak from the head of Dean's cock and he wants to lick it more than anything in the universe. As if Dean can hear his thoughts  he runs and thumb through it and licks it off as he winks to the camera. Only spurning Castiel's hand on moving faster, twisting slightly at the head and playing with his balls with the other hand.

  
Dean strokes himself faster and by the noises he's making he's getting close. “Fuck boys, wish this was one of your fat cocks in me, so good gonna cum all over these panties.”  _ Nnnngh _ “right there, fuck.” He shoves his cock back into the panties and strokes in earnest.

  
Breathy moans and grunts come quicker and Castiel's hand mimics the speed of Deans on the screen.  Before he knows it Castiel feels the white hot heat of his orgasm crest and he spills over his hand while he watches Dean reach his peak.  He can see some cum escape the top of the panties but as he comes down from his high the wet spot spreads along them and it's beautiful.

  
“Fuck that was good, let me get this out. Okay, lets see how ruined these are” He tosses the toy aside and gets on his knees for a close up on camera rubbing his hand over the mess under the satin. Smearing it into himself, his skin, pubes, through the fabric.

  
Castiel feels boneless but props up watching Dean, he mimics and rubs his spunk into his own pubes and skin.

  
“Hope you guys enjoyed the show, I know I did. Thank you, thank you for the tips and now I need to clean up, grab a snack, and pass out. Check out my profile for my snapchat, remember you gotta pay to get access but I promise you get some good stuff. I'm not sure when I'll be back on but I'm home for a few days so I'll probably see you later this week boys.” With another wink and a kiss the screen goes black and pop ups being offering other live channels.

  
Castiel closes his laptop and cleans up, while he does not need to sleep he decides tonight he wants to after what had to be one of his most satisfying orgasms to date. He reluctantly gets up and puts on some PJ pants and a t-shirt and curls up under the covers dreaming of light blue satin & lace and his best friend.


End file.
